Renowned as the heart of Virginia’s Hunt Country, Middleburg offers a variety of equestrian events throughout the year, including the Middleburg Spring Races and Virginia Fall Races. But it’s also a well-known destination for the arts with events such as the Middleburg Film Festival, Shakespeare in the ‘Burg, Art in the ‘Burg and more. And, of course, Christmas in Middleburg draws thousands of visitors, who line the streets each year to watch the parade and the Middleburg Hunt & Hounds Review. Check the calendar below to find out what’s happening around town.

2017’s Can’t-Miss Events:

May 27-28: Hunt Country Stable Tour

June 5-11: Upperville Horse Show

Oct. 14: Virginia Fall Races

Oct. 19-22: Middleburg Film Festival

Dec. 1: Christmas Tree Lighting

Dec. 2: Christmas in Middleburg

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May 2017

Memorial Day Weekend at Three Fox Vineyards

May 26 - May 29

Three Fox Vineyards, 10100 Three Fox Ln.
Delaplane, VA 20144 United States
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Three Fox Vineyards

Break out the Spectators and summer clothes! Expect a fabulous start to the summer season this Memorial Day weekend at Three Fox Vineyards. Bring your picnic, your family or friends and have a ball. Play bocce or corn-hole. Check out our picnic meadow and hammocks or stroll our woodland trails or the banks of Crooked Run. On Saturday, Pamela Anderson will be here with her Stella & Dot jewelry and the Exaggerations will be playing live music from 1:30-4:30 p.m.!…

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Memorial Day Weekend at 50 West

May 26
|Recurring Event (See all)

An event every day that begins at 12:00am, repeating until May 29, 2017

50 West Vineyards, 39060 John Mosby Hwy.
Middleburg, VA 20117 United States
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On Memorial Day weekend, we remember those who have made the ultimate sacrifice for our country. We celebrate the freedoms that we have because of their bravery. 50 West would like to invite you out Memorial Day weekend for fun in beautiful Middleburg with live music and great wine! Here’s what’s coming up for the weekend: - Friday, May 26th: Friday Night Flights - Saturday, May 27th: Far Away Songs performing from 2-5 p.m. - Sunday, May 28th: David Davol…

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Andre Pater: In a Sporting Light at the National Sporting Library & Museum

May 26 @ 10:00 am - 5:00 pm
|Recurring Event (See all)

An event every week that begins at 10:00am on Sunday, Wednesday, Thursday, Friday and Saturday, repeating until August 13, 2017

National Sporting Library & Museum, 102 The Plains Rd.
Middleburg, VA 20117 United States
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Andre Pater (Polish/American, born 1953) "Demonstrative," 2014, oil on canvas, 28 x 22 inches Private Collection, © Andre Pater

Andre Pater (Polish/American, born 1953) "Demonstrative," 2014, oil on canvas, 28 x 22 inches Private Collection, © Andre Pater Works from collections across the country are represented in the museum’s retrospective exhibition, “Andre Pater: In a Sporting Light.” The bold and vibrant compositions of contemporary sporting artist Andre Pater (Polish-American, b. 1953) are often compared to those of the great 20th-century British sporting artist Sir Alfred Munnings. “Go beyond the mere image, and the painting becomes a ‘matter of light,’” notes sporting art…

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Open Late at the National Sporting Library & Museum

May 26 @ 6:00 pm - 8:00 pm

National Sporting Library & Museum, 102 The Plains Rd.
Middleburg, VA 20117 United States
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National Sporting Library and Museum Middleburg VA Open Late

Please bring your chairs and join us for great music, family fun, and food from Hammerdown BBQ on the National Sporting Library & Museum Lawn. Concerts and Museum admission are free and open to the public 6-8 p.m. Picnics are welcome but no glass containers or outside alcohol is permitted. Cash bar featuring wine from Greenhill Winery & Vineyards and beer. Artist Andre Pater will join us for the concert, where he will be signing catalogues and prints. Performing: The After…

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Concert on the Lawn at Greenhill Winery & Vineyards

May 26 @ 6:00 pm - 8:00 pm
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One event on an unspecified date at 6:00pm

Greenhill Winery & Vineyards, 23595 Winery Ln.
Middleburg, VA 20117 United States
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Greenhill Winery & Vineyards

Enjoy music by Alan Gant on the lawn outside Greenhill's tasting room!

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Memorial Day Weekend at 50 West

May 27
|Recurring Event (See all)

An event every day that begins at 12:00am, repeating until May 29, 2017

50 West Vineyards, 39060 John Mosby Hwy.
Middleburg, VA 20117 United States
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On Memorial Day weekend, we remember those who have made the ultimate sacrifice for our country. We celebrate the freedoms that we have because of their bravery. 50 West would like to invite you out Memorial Day weekend for fun in beautiful Middleburg with live music and great wine! Here’s what’s coming up for the weekend: - Friday, May 26th: Friday Night Flights - Saturday, May 27th: Far Away Songs performing from 2-5 p.m. - Sunday, May 28th: David Davol…

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Andre Pater: In a Sporting Light at the National Sporting Library & Museum

May 27 @ 10:00 am - 5:00 pm
|Recurring Event (See all)

An event every week that begins at 10:00am on Sunday, Wednesday, Thursday, Friday and Saturday, repeating until August 13, 2017

National Sporting Library & Museum, 102 The Plains Rd.
Middleburg, VA 20117 United States
+ Google Map
Andre Pater (Polish/American, born 1953) "Demonstrative," 2014, oil on canvas, 28 x 22 inches Private Collection, © Andre Pater

Andre Pater (Polish/American, born 1953) "Demonstrative," 2014, oil on canvas, 28 x 22 inches Private Collection, © Andre Pater Works from collections across the country are represented in the museum’s retrospective exhibition, “Andre Pater: In a Sporting Light.” The bold and vibrant compositions of contemporary sporting artist Andre Pater (Polish-American, b. 1953) are often compared to those of the great 20th-century British sporting artist Sir Alfred Munnings. “Go beyond the mere image, and the painting becomes a ‘matter of light,’” notes sporting art…

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Free

Andre Pater Talk: The Iroquois Hunt and hound paintings at the National Sporting Library & Museum

May 27 @ 2:00 pm - 2:30 pm

National Sporting Library & Museum, 102 The Plains Rd.
Middleburg, VA 20117 United States
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Andre Pater National Sporting Library and Museum Middleburg VA

Andre Pater (Polish/American, born 1953) "Demonstrative," 2014, oil on canvas, 28 x 22 inches Private Collection, © Andre Pater Andre returns to give guests a guided tour and share his inspiration for creating many of the pieces included in the exhibition "Andre Pater: In a Sporting Light," specifically those focusing on the Iroquois Hunt Club. Catalog and print signing to follow. Admission is free. Please register to Anne Marie Barnes, Clarice & Robert H. Smith educator, at abarnes@nationalsporting.org, 540-687-6542 ext. 25.

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Spring Sweets Cooking Class at Salamander Resort & Spa

May 27 @ 2:00 pm - 4:00 pm

Salamander Resort & Spa, 500 N. Pendleton St.
Middleburg, VA 20117 United States
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Sugar is in the air as local berry season is in full swing! Learn how to create your own delicious fruit desserts just in time for your Memorial Day get-togethers or picnics.

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Art a la Carte at Salamander Resort & Spa

May 27 @ 3:00 pm - 5:00 pm
|Recurring Event (See all)

An event every week that begins at 3:00pm on Saturday, repeating until June 17, 2017

Art Salamander Resort and Spa Middleburg VA

Spend your Saturday afternoon discovering a new talent or honing your skills in a new way, under the direction of artist Mary Jennings. Choose one theme for the day; first guest to sign up determines what class will be offered. Two-person minimum. For reservations, please call 540-326-4060.

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